(Z)-hex-3-en-1-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 16.6 g of sodium hydride (purity: 60% or more), 600 mL of tetrahydrofuran was added and the resultant reaction mixture was cooled down to 0° C., followed by dropping 40.1 g of 3-hexen-1-ol into the reaction mixture at 4° C. or less to be added. After the completion of the dropping, the resultant reaction mixture was stirred at room temperature for 3 hours. Then, the reaction mixture was cooled down again to 0° C. and into the reaction mixture, 18.4 g of 2,4,6-trichloro-1,3,5-triazine dissolved in 120 mL of tetrahydrofuran was slowly dropped at 15° C. or less to be added. At room temperature, the reaction was effected over one night and to the reaction mixture, water was added, followed by extracting the resultant reaction mixture with ethyl acetate. The extract was washed with water and was dried over anhydrous sodium sulfate and from the extract, the solvent was distilled off to obtain 33.1 g of a crude product. The crude product was purified with a column (ethyl acetate:hexane=1:10) to obtain 23.22 g of 2,4,6-tri(3-hexene-1-oxy)-1,3,5-triazine which is the objective substance as a transparent oil. Yield: 61%, Purity: 98.6% (GC) the resultant reaction mixture at 4° C. or less to be added After the completion of the dropping, the resultant reaction mixture was slowly dropped at 15° C. or less to be added was added by extracting the resultant reaction mixture with ethyl acetate The extract was washed with water was dried over anhydrous sodium sulfate and from the extract the solvent was distilled off to obtain 33.1 g of a crude product The crude product was purified with a column (ethyl acetate:hexane=1:10)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 16.6 g of sodium hydride (purity: 60% or more), 600 mL of tetrahydrofuran was added and the resultant reaction mixture was cooled down to 0° C., followed by dropping 40.1 g of 3-hexen-1-ol into the reaction mixture at 4° C. or less to be added. After the completion of the dropping, the resultant reaction mixture was stirred at room temperature for 3 hours. Then, the reaction mixture was cooled down again to 0° C. and into the reaction mixture, 18.4 g of 2,4,6-trichloro-1,3,5-triazine dissolved in 120 mL of tetrahydrofuran was slowly dropped at 15° C. or less to be added. At room temperature, the reaction was effected over one night and to the reaction mixture, water was added, followed by extracting the resultant reaction mixture with ethyl acetate. The extract was washed with water and was dried over anhydrous sodium sulfate and from the extract, the solvent was distilled off to obtain 33.1 g of a crude product. The crude product was purified with a column (ethyl acetate:hexane=1:10) to obtain 23.22 g of 2,4,6-tri(3-hexene-1-oxy)-1,3,5-triazine which is the objective substance as a transparent oil. Yield: 61%, Purity: 98.6% (GC) the resultant reaction mixture at 4° C. or less to be added After the completion of the dropping, the resultant reaction mixture was slowly dropped at 15° C. or less to be added was added by extracting the resultant reaction mixture with ethyl acetate The extract was washed with water was dried over anhydrous sodium sulfate and from the extract the solvent was distilled off to obtain 33.1 g of a crude product The crude product was purified with a column (ethyl acetate:hexane=1:10)

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Hex-3-en-1-ol (179 g), crotonic acid (181 g), PTSA (7.2 g), and toluene (250 mL) were charged into a 2-L reaction flask fitted with a mechanical stirrer, a thermocouple, a Dean-Stark trap, and a condenser. The reaction mixture was heated to reflux at about 120-130° C. Water was removed azeotropically. The reaction was aged at reflux for about 4-5 hours until no more water evolved. The reaction mixture was cooled to room temperature and quenched with water (400 mL). The organic layer was separated and subsequently washed with sodium carbonate (5%, 300 mL), and further distilled to provide but-2-enoic acid hex-3-enyl ester (247 g) with a boiling point of 109° C. at 20 mmHg. fitted with a mechanical stirrer The reaction mixture was heated Water was removed azeotropically at reflux for about 4-5 hours until no more water The reaction mixture was cooled to room temperature quenched with water (400 mL) The organic layer was separated subsequently washed with sodium carbonate (5%, 300 mL) further distilled

Conditions: temp:125.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Hex-3-en-1-ol (179 g), crotonic acid (181 g), PTSA (7.2 g), and toluene (250 mL) were charged into a 2-L reaction flask fitted with a mechanical stirrer, a thermocouple, a Dean-Stark trap, and a condenser. The reaction mixture was heated to reflux at about 120-130° C. Water was removed azeotropically. The reaction was aged at reflux for about 4-5 hours until no more water evolved. The reaction mixture was cooled to room temperature and quenched with water (400 mL). The organic layer was separated and subsequently washed with sodium carbonate (5%, 300 mL), and further distilled to provide but-2-enoic acid hex-3-enyl ester (247 g) with a boiling point of 109° C. at 20 mmHg. fitted with a mechanical stirrer The reaction mixture was heated Water was removed azeotropically at reflux for about 4-5 hours until no more water The reaction mixture was cooled to room temperature quenched with water (400 mL) The organic layer was separated subsequently washed with sodium carbonate (5%, 300 mL) further distilled